Trifluoroacetic acid → 3-(6-Chloro-1-cyclopropyl-2,3-dihydro-1H-inden-1-yl)-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561626Notes

Reaction equation

FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][C:15]2([CH:19]2[CH2:21][CH2:20]2)O)=[CH:11][CH:10]=1.[CH3:22][S:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:33]=1[NH:32][CH:31]=[CH:30]2.[Cl-].[NH4+]>ClCCl>[Cl:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][C:15]2([C:30]2[C:29]3[C:33](=[C:25]([CH2:24][S:23][CH3:22])[CH:26]=[CH:27][CH:28]=3)[NH:32][CH:31]=2)[CH:19]2[CH2:21][CH2:20]2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

0.03 ml (0.40 mmol) of trifluoroacetic acid was added to 70.0 mg (0.34 mmol) of the compound from Example 119A and 65.4 mg (0.37 mmol) of the compound from Example 8A in 1.6 ml of dichloromethane at 0° C., and the mixture was stirred at 0° C. for 4 h. It was diluted with dichloromethane and added to saturated aqueous ammonium chloride solution, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 52.4 mg (42% of theory) of the title compound.

Workup

customthe phases were separated
extractionthe aqueous phase was extracted with dichloromethane
dry with materialthe combined organic phases were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record: ord-72b05fdea2a448f39462c631b0ccae06
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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